In this chapter we explore the struggle between the use of the Dative case and the competing strategy featuring the preposition ad ‘to’ and the Accusative from Latin to Early Romance. Unlike the Dative, the prepositional strategy is semantically transparent, since ad ‘to’ has a clear allative meaning. We first consider the diachronic development of the roles involved in the Dative-marked complex within a chronological span ranging from Plautus to the Vulgate and show that competing manifestations featuring ad are conditioned by semantic factors, since the extension of the prepositional strategy can be better explained in terms of metaphoric and metonymic processes. We discuss the gradual expansion of the prepositional turn in Early Romance with a view to exploring the paths along which it gradually took over the functions traditionally associated with the Dative complex. Building on these data, the chapter assesses the theoretical implications for a better understanding of competing multifunctional devices that encode role complexes from a diachronic perspective and shows how a pool of synchronic variation can trigger and constrain linguistic change.